142: Ask My AI

142: Ask My AI


Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

Yesterday, I got to participate as the host for a conversation about why productivity is about a lot more than getting stuff done with Khe Hy—a very cool dude and the founder of Rad Reads.

I caught exactly 1 talk live—@visakanv's declaration that greatness requires positive deviance and friendship—and spent the rest of the time having some amazing conversations with friends old and new.

Will have much more on THESIS in a future edition!


👉 Links

  • Courage / Risk ⚡️ Rudolph the Reindeer as a lesson on punishing deviance
  • Relatable 🏋  The global fitness competition with 322,000 entrants that has something for every skill level
  • ADHD 🧠 Words that ADHDers will relate to ("hidy up")
  • Systematic ⚙️ The 11 laws of showrunning (could apply to product management and startup leadership equally well)
  • Generative 🤖 Quora is back with an app that lets you switch between OpenAI and Anthropic's generative AI models for free called Poe
  • Togetherness 🫶  Most of us feel 20% younger than we really are
  • Creative 👁️  33 eye-catching transitions between 2 video clips

🧠 Roll Your Own AI Chatbot

You've probably seen folks creating AI chatbots that are trained on a large body of knowledge from one source—Huberman Lab Podcast and Lenny's Newsletter both have chatbots (HubermanAI & lennybot) based on their material.

The idea is that we can combine the natural language abilities of LLM's like ChatGPT and use them to summarize or synthesize high quality information with less hallucinations or false information.

One company trying to build this kind of an experience for people with less technical ability is No Code AI Model Builder. The team launched out of an AI hackathon and has been steadily iterating their way towards multiple tools that help folks build AI-powered systems of their own.

I recently used their AskAI feature to ingest about a dozen articles I've written on resilience across Every, The Muse, and this newsletter to see how well it does. Here I've shared a number of the responses and my rating for how good it was.

It's free to get started though I don't think that'll last forever. If you want to give it a shot for yourself, just click here (I don't make any money from this, and I paid for a pro plan). Or keep reading if you want to see how it did on my content.

Chatting with my AI Chatbot

Q: How would you define resilience?

Resilience is the ability to adapt effectively in the face of adversity and change. It is a skill that can be developed with practice, and is not a trait or resource. It is not about being tough and never showing weakness, but rather being fluid and agile, expressing vulnerability, and owning up to mistakes.

10/10: This is a great answer. Probably because I took a lot of pains to define it in the text, but it summarizes that answer well.

Q: What are specific, practical steps I can take after experiencing a reorg?

After experiencing a reorg, it is important to act decisively, wrap up existing work quickly, ask questions, connect with new colleagues, share out relevant memos and past work, and identify key problems to address in the new area.

It is also important to focus on developing an internal "locus of control" by focusing on efforts in moving forward within the areas laid out by leadership, and not worrying about the stock price or potential deals/projects/launches that are out of one's hands.

Additionally, it is important to take steps based on the lessons learned to ready oneself for future organizational changes, such as organizing key documents and materials as one works on the new project, and staying abreast of major initiatives across the company.

Finally, it is important to recognize the danger of burnout and take steps to off-load projects and restore oneself before things get worse.

8/10: This is a pretty good answer but it's a bit long and could also more even more specific. The vagueness may be due to the fact that I wasn't more specific in my articles.

Creating a custom AI model from my writing on resilience

Try my chatbot (alpha)

Q: How can a startup founder cultivate resilience in their team?

A startup founder can cultivate resilience in their team by embracing the messiness of work, accepting that work is often chaotic, and controlling their attitude, presence, and dedication to their craft.

6/10: This is really about how a founder themselves can be more resilient, rather than their team, but I guess it couldn't really understand the difference.

Q: My startup failed. What should I do now?

After a startup failure, it is important to take steps in a new direction and rally toward a better future. Invest in education and self-compassion, and consider your motivation for starting the business in the first place. Take the opportunity to break out of old patterns and try out new rhythms and styles that might work for you.

8/10: It's not super specific to a startup failure but it's reasonable advice. Wish it would have connected to the fact that I had my own startup fail.

Q: What happened with Jason's first startup?

Jason Shen's first startup was a long-distance ridesharing marketplace that went through Y Combinator in 2011. After raising $1.3M, the startup encountered difficulties and Jason eventually left to take a job with the Obama administration.

9/10: A concise straightforward summary! Would have been ideal if there was a sentence in there about what those "difficulties".

Q: Has Jason ever experienced something that required resilience?

Yes, Jason has experienced something that required resilience, as he recounts in his series Rethinking Resilience.

4/10: Ok, true information but come on, there should be more relevant details here

Q: What kind of hardships has Jason faced in his career?

Jason has faced a baseless copyright infringement case, seeing his startup's bank account drop below zero during a fundraising period, layoffs, reorgs, hypergrowth, burnout, financial stress, illness, pandemics, supply chain upheaval, and difficulty finding an idea that all founders could agree on.

8/10: Rephrasing the question helped. This actually draws from a number of sources and pulls it together in a good way (though it got confused about supply chain issues, which I was describing as a general challenge).

Q: What happened when Jason got sued?

Jason was sued by a man for using a quote from him in a book without permission. He was forced to take down the blog post, withdraw the book, promise not to disparage the man, and pay him $40,000. He was unable to pay the full amount and had to work out a payment plan with four close friends who loaned him money. The man then sued dozens of others who had used the quote for motivational posters, forcing them to pay thousands to settle.

9/10: Everything is true though "without permission" is misleading as I quoted a very short excerpt of his with attribution so permission wasn't strictly speaking necessary. Still based on the text it's a good answer.

Q: Has Jason ever been laid off?

Jason Shen was laid off from Etsy in 2017 and from Meta in 2022.

5/10: I was not laid of from Meta in 2022 but looking at the source material, I don't flat out state that so I understand how the AI could have gotten confused. Also the answer feels a little short but I guess it was a yes or no question.

Q: What was Jason's experience getting laid off from Etsy like?

Jason was surprised when he was laid off from Etsy in 2017, as he had not seen it coming. He was offered severance, healthcare coverage, and other benefits. He then took a part-time product management role, gave a TED talk, and eventually closed a pre-seed round of funding for his own startup seven months later.

9/10: This is a pretty good summary of what happened after I was laid off, though the question really is asking what my experience was of the layoff itself. Still everything was factual and a good length. Nice job.

Q: What should I do if I'm feeling burned out?

If feeling burned out, focus on constructive coping mechanisms like getting adequate rest, time outside, and journaling, and avoid destructive ones like badmouthing coworkers, sabotaging projects, or disengaging all together. If feeling awful many months later, consider a larger life change outside of the workplace or guidance from a medical or counseling professional. To reduce power of negative feelings, try urge surfing, a mindfulness technique that starts by focusing attention on the present, through the breath. Show compassion to yourself and extend it to others on the team. Make specific requests for help from your network and lend a hand to others.

7/10: Given that I haven't directly written about burnout in the articles, it's a decent answer.

Overall: I think what this exercise has revealed is that your output is only as good as your input—this is true for both ChatGPT and a personal AI assistant. The more I can offer detailed concrete advice and strategies across a range of circumstances, the more effective this AI chatbot would be.

That said, building this experience was very easy—just paste in a link or upload a PDF and the model can very quickly incorporate that knowledge into the bot.

Give it a whirl and let me know what you think!

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